Winging It With Emma Isaacs

5 Oct , 2020 podcasts

Winging It With Emma Isaacs

CMO Emma | Winging It


So often, we feel the need to have all the answers. For Emma Isaacs, however, sometimes all it takes is to wing it and trust in ourselves and take bold steps forward into what we want to create. Emma is an Australian entrepreneur and the owner and Global CEO of Business Chicks, Australia’s business women’s community. She sits down with Katherine Twells today to talk about the concepts from her brand new book called Winging It and how she’s had to pivot and do some different things to thrive during a really challenging year.

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Winging It With Emma Isaacs

Trusting Your Power To Create And Shine

On the show, I am speaking with the remarkable Emma Isaacs. Emma is the Founder and Global CEO of Business Chicks. She’s originally from Australia but she is now living in Los Angeles. Emma counts Richard Branson as a personal mentor which is amazing. She is the author of a brand-new book called Winging It. We’re going to talk a lot about the concepts in the book in our conversation. If her incredible business success is not enough, she also has six children under the age of eleven. This is clearly someone who is making it happen in life in a very big way.

Emma is also a passionate philanthropist. Business Chicks has raised over $13 million for various nonprofits. Each year, her team produces events and content that reaches over 500,000 women with past speakers like Brene Brown, Nicole Kidman, Arianna Huffington, Diane von Furstenberg, and Gloria Steinem to name a few. This 2020, no one has been able to have events so she’ll talk about how she’s had to pivot and do some different things to thrive during a challenging year. I am very thrilled to share the conversation with Emma. You’ll find wisdom and insight as she shares her story with you. Often, we feel like we need to have all the answers but as Emma shares, sometimes, all it takes to wing it is to trust in ourselves and have the courage to release perfection and take bold steps forward into what you want to create. Let’s get to it. Please enjoy the conversation with the unstoppable Emma Isaacs.

Emma, I’m happy to have you as a guest on the show. Thank you so much for taking the time.

Thanks for having me. I’m excited for our chat.

Origin Story

It’s going to be great. I already know it. Let’s start here. At the beginning of the show, I always do a bio and tell people a little bit about your background but there’s always way more to the story than a bio, whatever it tells. What I love to do at the beginning of our conversation is to ground everyone on your origin story. Where did you come from? How did you get to where you are now? Share some texture on that with everybody.

Thanks, Katherine. I’m an Aussie. I’m a proud Australian and I moved to California a few years ago. I was born and raised in sunny Sydney and calling LA home. My backstory is that I’m what’s called a career entrepreneur. I’ve never worked for anyone else or taken a paycheck from anyone else throughout my career. It’s amazing in a lot of ways and it suddenly forces you to be creative with your path, how you make up rules for life, how you work out, how you’re going to be able to pay your rent, or pay your mortgage. As your life develops, how you’re going to be able to put food on the table.

It’s a very unique path that I’ve taken in not working for anyone else but I started out my career with my first business when I was eighteen years old. That was a little recruitment company that I started with a friend. We took that business from just the two of us when we started it to a healthy, small business of about 40 people. We had a beautiful culture, won a host of awards, and I love that business. We grew that into something special. Other people say, “How did you do that at the age of eighteen?” I truly had no idea what I was doing. Back then, life and business was a little bit simpler.

Be yourself, and you can't lose. Click To Tweet

I returned to the values that my parents instilled in me. That was all about being kind to people, very much working on relationships, and putting one foot in front of the other. That’s a little about how I got a start in entrepreneurship. After seven years of being in that business, a friend invited me along to an event run by an organization called Business Chicks. I said, “That’s the worst company name in the entire world. I would never go to anything that calls themselves chicks. I’m a feminist and I’m a professional entrepreneur. I’m not doing that.” She said, “You need to come along and you need to experience these things.”

I remember walking into my first event and being completely bowled over with the energy and the culture of this place, and I loved it. I ran back to my recruitment company and I passed her my credit card. I said to everyone there, “Let’s all become members of this organization. Let’s go to the next event.” At that next event, I learned the business was for sale. To make the long story short, I ended up buying that business. I was 25 at that time. I’ve been building the organization and we’re in two countries, eleven cities. Honestly, I’m still as excited about the business and the work we do. I love it. That’s a little about the back story.

When you bought it, did you consider changing the name?

That’s what we did. The business was founded in Australia and we have fifteen years of legacy there. It has a beautiful reputation with the largest of its kind in Australia. We do some amazing work. You’ve heard some of the speakers that we’ve been able to work with from Sir Richard Branson to Arianna Huffington, Gloria Steinem, Sarah Jessica Parker, and the list goes on and on. We have a beautiful reputation there. We’re truly the best in class in Australia. When I moved to America to start the business here, you should have been a fly on the wall about marketing meetings there because it’s not a name that resonates with everyone. When you understand the business and a little bit about the Australian nuances of not taking ourselves so seriously and being a little bit irreverent and cheeky, then you get it.

Many people can experience one of our live events which is happening. My learning in that is you cannot be for everybody. You have to dial-up what you do in your brand, you have to be proud of it, you have to live and breathe your values, you have to walk your walk and talk your talk. For us, that means being our brand and that is always going to be who we are. We have considered changing the name on many occasions, but we’ve arrived back at the answer of be ourselves, you can’t lose, and it’s not for everybody. Those who are drawn to it and those who aren’t. That’s cool too. There’s some other community for them.

That’s getting clear about what you want to be and being unapologetically out there living and promoting your brand. You have a legacy, so that’s amazing. A few things I want to return to in your origin story that are noteworthy and fascinating. You’re eighteen and you want to start a business. I’m always interested in what is it about certain people that give them that fire in the belly or that desire to do something like that when a lot of eighteen-year-olds are thinking about college or what I want to do with my life. They’re not thinking about that. You had this natural entrepreneurial desire. Why do you think that was?

CMO Emma | Winging It

Winging It: Our brand is always going to be who we are.


I don’t know that I had that intention as clearly as you may have. I never went through schooling and the little college that I did do. I never had this grand ambition to be an entrepreneur. I didn’t even know what the word meant for about 3 or 4 years into me having my first company. I didn’t start out with this intention, this would be my career and I needed to have a business. It was a series of circumstances that appeared and I went with them. I know we’re getting into talking about this philosophy of winging it. To me, winging it, which is what my book is called, is very much about exploring opportunity, looking at what’s in front of you, putting one foot in front of the other, and progressing even though you don’t have the answers.

That’s how I got my start, but even rewinding the clock a little bit further back to when I was eighteen, I come from a very middle-class background. We never had a lot of money but we had a beautiful childhood. I was the first of three kids. If you believe anything about birth order, I suppose I was the archetype or leader. My parents tell the story of me as a seven-year-old getting all the kids together from my neighborhood in the backyard. I’d bring them all together. I’d stand up on a step and I’d say, “Here’s what we’re going to do.” I was being a bit bossy back then even at the age of seven. I tell them to go to their parents’ houses, borrow some money from their parents and bring it back. We collected all the bills and the coins. I would go up to the nearby store and I would buy as much candy and chocolate as I could. We’d bring those packages back, unwrap them, package them up into smaller little bundles, and then sell them back to their parents. That was my first foray into making a profit and running a business.

Your childhood gives you a lot of clues about what you meant to be doing with your life. As I’ve grown and asked my parents more questions about what I was like, I always was the kid that was tugging on my mom’s skirt and asking a million questions. I always was curious. I never had this grand vision to be an entrepreneur. I met this woman socially and she said to me, “I have to start this little recruitment company.” I went along for an interview with her. At that time, it was her and her business partner. It was all very amicable that we parted ways and as he was walking out the door of that company, he turned around and said to the other woman, “If you’re going to offer equity to anyone in the world, you offer it to that kid sitting there.” That’s how I found myself as an eighteen-year-old 50% shareholder in this little recruitment company.

The not knowing is a beautiful gift. I didn’t have any expectations of what it was like to be a business owner. Naivety in business and sometimes leadership can be a beautiful thing as well. You are forced to be creative and do what feels right rather than progressing where there is a clear set of rules that have been handed down from someone else. I very much led from instinct and intuition. With building that company, I always talk about the colors on the wall were different from the colors of our logo. I got my dad in on the weekend and he painted the walls. We were all answering the phone differently. I read a little manual of how to answer the phone. It was the things that made sense to me at that time. That’s how I got my start.

You discovered as you went along and I do think it’s interesting your childhood story. There are many clues in our childhood. My twins are fourteen and one of them has a similar thing. They would buy candy and resell it to his friends at school. I see how his mind works. I see the entrepreneurial side of it. My other child is super compassionate. He’s always tuned in to other people. You can watch as a parent, “I see these seeds and these gifts in my children. How would they use them? What will they become in life?” Let’s talk a little bit more about winging it and getting unstuck. You mentioned rules for life and I’m a big believer that we set the stage by our belief system.

Winging It

Who do we think we are and what we think we can do can come in from family structures or culture. You shared about the fact that you allowed yourself to create and invent. You weren’t expecting to have all the answers. I have talked to a lot of women and men that there’s a concept of, “I have to know everything before I embark.” People get stuck where they are because their belief system doesn’t allow them to move forward. Can you talk a little bit about the concept of winging it further and how we might get unstuck?

For many years that I’ve been building Business Chicks, I’ve been in a beautiful position to consult, meet, work with and learn from thousands and thousands of mainly women who have shared with me what holds them back and what propels them forward. That’s the collective wisdom that led me to write this book called Winging It. Whilst men are still playing with imposter syndrome from time-to-time, it is women who suffer from getting stuck and waiting for permission, waiting to be tapped on the shoulder, and waiting for opportunities to fall on their laps. This is better than anyone in your work and I always talk about that women will see a job advertisement and think, “I’ve only got 6 or 7 of the qualifying criteria. There’s no way I’ll put my hand on that,” even 8 or 9. Who knows? Men will say, “I’ve got three of those. I’m going to apply.”

Your childhood gives you many clues about what you're meant to be doing with your life. Click To Tweet

My work has been a study of what holds people back. In parallel to that, I have been fortunate to spend a lot of time over the years of my working life with incredible people who have come into our business world and have been speakers for us. I’ve got to learn what makes people successful and what keeps them successful as well. This philosophy of Winging It, when I set out to write this book, that was the first two words that came to me because it’s been my life philosophy. As I said before, it’s definitely about how do you operate in an environment of uncertainty? As an eighteen-year-old kid, who has no business experience and has no idea what they’re doing, how do you progress and get to a level of success? As a mom who’s never had kids, how do you progress and find a level of mastery?

It all comes back to this notion of winging it. It’s moving forward in uncertainty. It’s putting one foot in front of the other. It’s about trusting your instinct and building your confidence muscle. It’s about having the vulnerability to say, “I do not have all the answers, but I am going to try and figure it out.” That’s one of the cornerstones of any great leader, having that position of vulnerability to be able to say, “I don’t know what we’re doing here.” The more and more I studied successful people, the more and more I found out that most people in some way or to some degree do not know exactly what they’re doing. Unless you’re a cardiothoracic surgeon. We want you to know what you’re doing.

The storm that we’re in now with COVID is a perfect example of leadership in vulnerability and being able to wing it with your people when we do not know where we’re going to be. Come April 2021, no one knows we’re going to be at the end of 2021. We honestly sit here and pretend to have the answers and the perfect roadmap that we are going to follow and we’re going to step through. It comes back to admitting your fallibility. We’re in this together. We’re going to step it through, do our best, and be kind to ourselves. That’s what the philosophy of winging it means to me. There are some elements of taking risks. To achieve any level of greatness is going to be a level of comfort with taking some risks. For me, winging it is about moving forward, despite having the rules and the roadmap for how it’s all going to pan out.

You don’t get there without courage. I do think that the title of your book is appropriate for what we’re going through and what’s interesting. This has come up in some of the other podcast conversations. We all live with the desire to control. It’s somewhat of an illusion but when I started getting stressed out, I cleaned out all my closets because I think I’m in control of my closet, but we really aren’t. Before COVID, you can put a plan in place, you’re going down and you think, “I understand my world.” The truth is we never knew what was going to be around the corner professionally or personally and we’re living that now.

What’s unique about the now is it’s a collective challenge. Before, you might have had someone who was in a smooth sailing period and another person going through a personal transformation or that chaos state. Now, we’re all in a bit of a state of chaos and it does require the skill of winging it. The vulnerability of that is huge. A lot of different people follow this show, some of them are business leaders and some of them are individuals who are leading themselves. Share more about how you lead and as we’re talking about this vulnerability in this time, how do you set the tone for people when there is higher anxiety, there are challenges through adversity? How do you do that for them?

It’s a huge challenge right now for any leader. In a lot of ways, I’m in a fortunate position because I have a wonderful CEO who runs my business. I’m always the one who’s going to lead the vision and she’s operationally in-charge of my business. We do a lot of work and invest a lot of time in who we want to be as leaders for our people during this time, what support they need, and showing up for them. That’s been a real focus for us. For me, it’s very much been a return to core values. We have always been a values-led business. If you’re in any of our team meetings, you would know that we always talk about them that even more so, this is an opportunity for us to return to what’s important to us as a business, an organization, and who we want to be as leaders.

I’m one of these leaders that always refers back and always rests on our core values because they are our north star to who we want to be personally in our businesses and organizations. A wonderful methodology that I’ve used throughout my career is paying attention to strengths-based methodology and trying to help my people understand what they’re good at and what they’re not good at. I’m sure you’ve done a lot of studying into strengths as well, but the basic concept is that when you came home from school when you were young, you might have got a B or C in math and your parents said, “You’ve got to spend all your time focused on math and getting better at it. This is not good enough. Why can’t you do this right?” The strengths-based methodology will have you say, “You’re good at English, literature or whatever. Let’s dial that skill up.” For me, core value is a real focus, hiring people to their strengths and indeed spending the majority of my day working to my strengths as well.

CMO Emma | Winging It

Winging It: Winging it is very much about exploring the opportunity, looking at what’s in front of you, and putting one foot in front of the other and progressing, even though you don’t have the answers.


In terms of specifically working through COVID and our leadership, it’s been very much about communicating more with our people and trying to carve out time for one-on-ones with key people that might look like they’re not coping as well as others. We’re trying to have availability for our people as well as communicating more from a business perspective with our customer base. We make money through our membership models. People subscribed to it become Business Chicks members. We make money through our live events model which is being completely decimated for the moment. We also run beautiful B2B business brands, sponsor activities, and we do campaigns with them. One of the first decisions that we sat down after lockdown started, we started to come to grips with the enormity of this problem that we’re all facing.

We employed early and urgent action. We sat down and we said, “What needs to change? Who do we want to come out of this being?” That was a great philosophy to start with when this is all over. It is going to be over perhaps a lot longer than we originally thought, but it will be over one day. What do we want people to say about us when we leave the room? Who were we as leaders during this time? That’s our leadership styles during COVID for our community, we realized we’re going to be working remotely and from home. How could we meet them with their needs of connections?

We started looking at a number of different event products like meetups online. We pivoted all our life events to digital delivery which was another moment of winging it because we’d never known how to do that. We had to figure that out in a couple of days which we did beautifully. It’s very much about showing up and being seen. We didn’t hide. We just start up like, “Here’s what we know.” Most of it we don’t know. How can we make an impact in this time? How can we meet the needs of our members? How can we meet the needs to our people? How can we do it in a humble way that shows people that we’re all in this together? As leaders, we need as much support as you guys do as well. Let’s just put one foot in front of the other and try to work this out together.

It’s important as leaders that we express the fact that we’re figuring it out as we go to and there isn’t some hidden secret manual that we have. I would love it if we have that and said, “Here’s what to do next.” If it were that way, it wouldn’t be very interesting. We develop our mental muscles by walking through adversity and having the courage to do that. There were a few things that stood out to me about what you said. Taking early and urgent action, being seen and being present. There’s nothing more valuable than your gift of presence. “Thinking about the end in mind,” to quote Stephen Covey like how do you want people to think about you when all is said and done during this time?

Core Values

The other thing that is interesting is this core value conversation. In my last conversation with Peter Sheahan, we talked a lot about alignment, and the difference between agreement and alignment. This alignment piece is that the rules of life and the rule for businesses within your team that everyone is on the same page so that you can move forward as a collective. It sounds like you’ve hit all of those things quite beautifully where other organizations are not thriving. You have continued to have a thriving organization by figuring this out. Kudos to all the things that you’ve done to navigate these uncertain waters.

It’s not without many failures along the way. We had to rationalize and make a few layoffs at the start of the pandemic which was challenging as leaders. We are very much a people-based business. We love and care for our people dearly. I have a number of people in my business who have been with me for over a decade. I have a number of people in my business who have done 4 or 5 years with me. They’ve gone to spread their wings elsewhere, come back two years later, and did another three years. We are very much a people-focused and a people-based business but as a leader, you have to make tough calls.

Leadership is not about always being liked. It’s having to protect the culture of a business and protect the health of the business so that the jobs for everyone else is still there in the future. What we’ve spoken about up until this point is we’re proud of it. We are core values-based, strengths-based, people first, and all of those things, but we also have to ensure our viability as a strong brand and a strong business moving forward.

One of the cornerstones of any great leader is having that position of vulnerability to say, “I don't know what we're doing here.” Click To Tweet

Sometimes as leaders, that takes having tough conversations and making unpopular decisions. We’ve not been immune to that because from an events perspective, 85% of our revenue was taken away in that line item. It’s huge. It might all sound rosy but it has not been. Getting back to our why, our core values, communicating more or this relentless optimism that we will get through this. As leaders, your people are looking to have that optimism, sense of hope and a sense of grace. That’s something that we have tried to focus on whilst the business has been shattered in that area.

You mentioned failure. Even though from the outside, people as an individual or as a business look like everything is working and they’re having successes, that doesn’t come without trial and error. At Coke, we talk about it as having a growth mindset. The growth mindset is fail, learn and try again. There’s no perfection in this process. It’s muscling your way through and growing in that process. How would you share more about your approach to failure and how that’s enhanced your success in the long game?

I don’t enjoy failure one bit. I’m quite a driven and ambitious individual. I struggled with the concept of failure, but I have learned to be grateful for the failures that I’ve had and there have been many. In the journey, we all know that it’s a cliché but it is full of road bumps and ups and downs. You have to be the first to get up and pick yourself up. I remember a mentor describing being an entrepreneur is being like a punching bag. You get punched from every which way and you’ll have to fall down. You’ll have to pick yourself back up again. I’ve tried to exercise that muscle and tried to listen to the time that I’m on the ground floor. I’ve had a number of failures throughout my business career. Most of them come back to a lack of focus.

Early on in my career, I remember I was running Business Chicks and it was going well. We were profitable and we were growing. We moved into this cute two-story office in Australia back then. We didn’t need both the floors. I thought we’ll put all our people on the top floor and we had this free space down below. I’ll start another business there. I started this little fitness studio and it was a complete flop. I wasn’t passionate about it at all. My passion was in my original business and it was a waste of everyone’s time. That was a good lesson in failing. The lesson for me was you need to focus on whatever you’re doing and have that linear vision for where you’re going.

That was one place where failure showed up. I’ve released this book in America and I got rejected by 47 publishers which is beautiful. It’s a humbling experience when you immigrate from one country where you’ve achieved a level of success and you move somewhere else and you’re completely unknown. I’m not going to say the failure and the rejection didn’t hurt every single time but it does make success most weight. My relationship with failure is something that I’ve gotten better at over time. Something that I’ve been deeply introspective about, trying to not move on from sitting in the failure and going, “This feels icky and it feels yuck. I don’t want to be here,” but “Why is it here and what lessons do I have to take into my future self in order to make the failure useful?”

Work-Life Balance

Everything is our teacher. There’s no question about it. You mentioned the punching bag of the entrepreneurial journey. This resilience, this grit, and the ability when you’ve been knocked down for the 3rd, 4th, 5th, 6th, 7th time and you get back up. Whether it’s our personal challenges during COVID or business challenges, it’s the people that keep getting up and walking forward. New gifts will emerge. New things will happen with that. As we’re talking about this, we are whole people. There’s the business journey and there’s a personal journey. For our audience who don’t know this about you, you have six kids under the age of eleven. For anyone who read that, they probably got exhausted and say that it’s a lot. Here you are juggling this incredible global business, and you’ve got your kids and your family. I’ve spoken a lot at different times about work-life balance. The fact that that’s a myth. There’s a harmony and a wholeness about that. Would you talk about how do you manage all of this? How do you do it?

There are many moments that I don’t manage it. I like to say that my favorite game to play with the kids is hide and seek because I can go and hide in my closet for a couple of minutes and not have anyone to disturb me. Parenting six young kids, my kids range from 11 down to 3 months. I had a new little guy and he’s gorgeous. He’s a real little gift. It’s exactly as you’d imagine, it’s completely chaotic and crazy. Our household has never ever had a moment of silence, has never ever a moment where someone is not crying or yelling out for me. Coming back to this philosophy of trying to work on how to be in chaos and be positive when everything else might appear to be negative.

CMO Emma | Winging It

Winging It: Stop Thinking, Start Doing: Why Action Beats Planning Every Time

I learned a lot of skills from my business journey that I’m applying to my parenting. Things about being organized, managing time, being calm, and all those things is in full of my parenting journey. It is a lot and I like the saying that says, “Even though I carry it well, it doesn’t mean that it’s not heavy at times,” because it is. My version of doing it all is I never shy away from telling the truth that we have help. I have a babysitter in the mornings and afternoons. That does not mean for one second that I ever am sitting on the sofa with my feet up. I’m a very hands-on mom and present parent to my kids. You have to be particularly in this time where four of them are in virtual learning and me running around to teach them and trying to figure out. You know all about it. It’s a wild time.

That all sounds great. I say that would be useful for some people reading. What I’ve gotten good at over the years of both being a parent and running a business is learning how to say no, guarding my time, and prioritizing my time as my greatest assets. In the book, I talk a lot about this in the chapter on parenting and time management. This is a theory. I’m not sure if you’re familiar with it but it’s called The Four Burners Theory. What we do is we imagine our lives as there are four burners going. One is your work, one is your family, one is your health, and one is your friends. It’s been said that to be successful, you have to turn one of those burners off altogether. To be successful, you have to turn two of those burners off. What does that look like for me is I am so focused on my family, my work, and everything else.

I have a small bunch of friends, we have an amazing relationship but I don’t have 100 people that I’m trying to catch up with every weekend. I don’t have the capacity for that taking on what I do in my work, as a mother of six young kids, and my health. I used to run most days and I used to have a personal trainer but all of that is full into the wayside. For me, it’s prioritizing my family and my work above all else. I’m not running marathons. I’m not going away with girlfriends for weekends. I’m not resentful about that either. I’m clear about what I want to get up to in the world. I’m clear about my vision for both my family and my business. I always say you can’t be a victim of what you choose.

I chose to have this company that is doing amazing work. I chose to parent these six little kiddos. I do try and bring a huge amount of gratitude into my life every single day. Whenever it gets overwhelming and stressful, I remind myself that right now touch wood but I have six very healthy kids and my business has survived. I know we’ll do well and pull through this. Not to get woo-woo on you but this practice of gratitude is important. I try and let that dictate my day every day. It gets me through those moments where I want to hide in the closet and run away from them all.

We all have moments where hiding in the closet is called for. I appreciate you sharing that. The people reading will appreciate you sharing that because we are making conscious choices. Sometimes, we look at people and we think for ourselves that we need to be doing all these things. There’s a long list of I need to be exercising. There’s only so much time and energy. I’ve also had conversations with people around the power of presence because people will say, “When I’m with my family, I feel like I’m neglecting work. When I’m with work, I feel like I’m neglecting family.” You end up being nowhere. You’ve not where you are. It’s the ability whether it’s with one of your children or one of your team members to be there, and to accept that when you choose, you had to choose between the workout facility. You were fragmenting yourself. When you make a choice to be present to what’s happening, that is a tremendous gift. There’s so much more energy created. At that moment, the other things have to fall away until it’s their turn. It’s a practice we all are trying to get better at.

You’re right, we call it a practice because it is a practice. We have to practice it every single day. We have to try and get a little bit better at it every day. For me, this myth about work-life balance is an unattainable ideal. The narrative around it leaves us this feeling less than all the time. As you said, when you say work-life balance, I get this image of someone standing there with these two scales. They have to be perfectly tipped at the right balance to make us feel like a whole human being. There are going to be times when the scale is going to take up here and I have to be focused on my work and my parenting stuff is for the next couple of hours or whatever.

It’s about being kind to ourselves. It’s about having an acceptance of that. It’s not striving to this perfectionism and this idea that we’re told we have to strive for it because it is unrealistic. The power of presence is everything. I tried it. It certainly has been something that I’ve gotten quite good at over the years. When I’m on a call, she’s on a call, and she’s doing that. When she’s on the floor playing blocks, she’s doing that. Every now and then, I’ll slip and I’ll have to take a call or I’ll have to check my phone, but when I’m with my kids, the phone is away. I’m trying to be there with them. When I’m in my office working, the door is shut and mommy needs to work. That’s the guidelines. They’re the boundaries that we have to set.

Leadership can be a really beautiful thing because you are forced to be creative and do what feels right. Click To Tweet

There’s no question and just like you, we’re intentional about how you wanted to come out of COVID. You’re also living intentionally about what life you’re choosing and how you want that life to unfold, which is powerful. With COVID too, it’s also teaching us that there are different ways to do things. There was the old model about do we need to travel, get on the plane, be at this meeting and do that. We’re learning new things. While the challenges have been real and significant for a lot of people, I’ve also seen that there have been some gifts whether I’m on Zoom calls and my sons are on calls with school but we’re having lunch together. We’re spending more time together. I’m also able to feel connected in a lot of my one-on-one calls with people and having good conversations so I’ve seen the gifts. What have been some of the gifts for you during this time that you’ve discovered for yourself?

Tremendous gifts. You summed that up beautifully. For me, my life pre-COVID was racing to LAX and jumping on planes in New York, and three days away from the family or worse, jumping on a plan to go into Australia for two weeks which is what I had to do regularly. The re-imagining of what’s possible has been a beautiful experience. Getting back to what’s important, I’d like to think there’s a greater meaning to all of this. I have found a heap of beauty and joy in the lessons. I don’t want to downplay for a minute the suffering and the pain in the world because it’s massive. Kudos and hats off to anyone who is working on the frontline or anyone who’s suffering from personal experience.

For those of us who do enjoy the privilege of having a roof over our heads, a career that we love, and having a family that we need to care for. I don’t, for a second, minimize that. There’s a huge amount of privilege in that. My hope is that we will remember this and we will not race back to the way things were. We will not race back to LAX to jump on the plane to go to New York for that business trip. We will remember this time as being one that slowed us down and recalibrated priorities. It got us back to who we are as people. From a business perspective, I’ve appreciated the opportunity. As an entrepreneur, that’s what I do for business.

We return to being scrappy and getting back to, “Let’s forget everything that we know. Let’s unlearn what we know about this business. Let’s return back to how do we make money. Let’s simplify this.” I’ve always said there’s a huge elegance in simplicity in business. I often say to people, business is quite easy. It’s the human mind that complicates it but you have to earn more than what you spend. It’s quite simple but we forget that. For me, the return to being a leader who simplifies things and gets clear on, how do we make money here? What leaders do we have to pull? How can we turn on that and tap when needs be?

That’s been a beautiful gift for me as well to getting back to my roots of making it up and I suppose winging it. It’s completely unprecedented and I’ve loved that. That to me professionally has been a big gift as well. Don’t we? I know you do it in your work. I’m sure your team does it in their work. You can operate from a baseline of complacency like we’re doing well and everything is ticking along. That’s not where the magic happens. The magic happens at the extremes. We’re living at the extreme. We’re living on the edge of the cliff right now. As you said, there’s a massive amount of beauty in that. I want us all to remember that, hold these lessons, and take them with us moving forward.

That’s beautifully articulated and I could not agree more. I’d like to believe that we will take a lot of this with us. We are co-creating our future together with the decisions that we make as an individual and as a collective. I love what you say, the elegance of simplicity. In many ways, our lives became complicated. There are lots of distractions. Technology is a gift but also creates a distraction. There are a lot of things. I do believe this time has given us a chance to perhaps step back and crystallize some things a bit differently, and think about how we move into a new place.

I love everything that you’ve been sharing in this conversation and we’ll be winding it down. Otherwise, I would keep you for the day. I want to round out with one general question. As you think about your journey, you shared your origin story, and all the ways you’ve been winging it through your life and creating some amazing things. You’ve shared so much already, but is there a piece of wisdom or something that’s had an impact on you? Maybe a teacher, a friend, or a mentor has shared with you along the way that you could share with people reading or something that stands out for you that could be a guide for people.

CMO Emma | Winging It

Winging It: Leadership is not about always being liked. It’s having to protect the culture and health of a business so that the jobs for everyone else is still there in the future.


That’s a beautiful opportunity. For me, the greatest theme and the greatest teacher in my career so far has been the importance of relationships, human connection, and seeing people like we started the conversation with. How I’ve been able to build my business is definitely through putting effort, time, and investment into my relationships. Some people call that networking, community or relationships, but people have always been the one thing that I invest the most time in. I’m known as someone in my business that will sit down and write 600 holiday cards at the end of the year. I remember being in my office a couple of years ago and a new employee walking past.

It got back to me that that person had said, “Why is she doing that? She should get someone to do that for her. That’s a ridiculous use of her time.” That common sense would dictate that a founder or CEO should not spend that time writing 600 holiday cards. I said to that new employee, “This is my work. This is what is important to me. This is how we’ve been able to build this community. It’s through the relationships that we have, the kindness we show, and who we are as leaders. This is who I want to be as a leader and I want to remember the detail. I want to be there for people. I want to do more favors for others than they’re doing for me.”

I always love what Dr. Lois Frankel says about this, “When you need a relationship, it’s too late to build one.” I believe that if I can impart any wisdom, we should always be working on our relationship. We should be investing in others, building our networks, and thanking people for what they taught us. That’s been the guiding light for my career and something I’m not going to give up. I’m not going to give up writing 600 holiday cards. I’ll be doing 1,000 this 2020 because this year has been about the power of connection. We have learned that it doesn’t necessarily have to be in person for it to matter as much. Relationships is the key thing. It’s something we should all work at and invest time in.

Well said and the 600 to 1,000 cards is another way to make me tired thinking about it, but it’s another way to show your presence. It’s personal and you’re investing. The origin of this show with the CMO Summit is about community. The whole idea that this is not a solo journey, this is a journey for all of us to come together and find out how to help each other. We are a part of a collective and the actions that we take makes a difference on other people. It’s going to make a difference in what we do moving forward.

Can I say one more thing on leadership because your show is very much themed around leadership? Often, we think leadership lives in other people. We look up to people and think they will lead the way and it’s their job to show us the way. We all have to understand that there’s a leader in every single one of us. It is up to us to step up and to show up no matter what our title is, no matter what our salary packages, no matter what our experience is. I firmly believe that you can be a leader as a young eighteen-year-old kid not knowing what you’re doing. You can be a leader as a CEO. You can be a leader at every single level. It’s important for people not to sit back, rest, and say leadership is for my leader. Leadership is something that we all need to lead into and practice on daily. I know you and your audience know that, but it’s a good little reminder for us as well.

It’s an important reminder. I often find that people underestimate their personal power and the impact they can make. Sometimes, we defer to others but we can make a huge difference in what we choose. Emma, thank you so much for your time. I’m so grateful.

I’m grateful for the opportunity. Thank you so much for inviting me and for having me.

An entrepreneur's journey is full of road bumps and ups and downs; you have to be the first to get up and pick yourself up. Click To Tweet

Emma, this has been such an incredible pleasure to speak with you. I want to say thank you for your generosity of wisdom and everything you’ve shared with our audience in this conversation. It’s been wonderful.

Thank you so much, Katherine. Thanks for your time.

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About Emma Isaacs

CMO Emma | Winging It

I’ve been winging it my whole life. I dropped out of college after six months and started my own company at 18. I bought Business Chicks a few years later (even though everyone told me not to) and grew it into what it is today: a global community of women who cheer each other on.


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